Hey beautiful human,
Here's where I'm standing today.
Last week I did four live events, and I loved every minute. That's the thing I know for sure now: live is where I come alive. Talking to people, sharing in real time, the energy going both ways - me giving, them giving right back. That's where I do the most good. That's where I make the biggest difference.
And at the same time, this keeps coming up for me. This whole bigger-better-faster-grow-scale world, where everyone's racing to make the most money for the least actual value. I don't like it. It doesn't fit who I am.
But I'm not naive about it either. I have to build something that serves people without burning me down to the studs - and still pays the bills. So here's my actual philosophy: I'm building a business I can do for the rest of my life.
I'm 57. If I'm lucky, I've got another twenty years or so. And I'm building this on the far side of two years unemployed, staring down bankruptcy, watching my 401k drop from a hundred and twenty thousand to thirteen. There's no nest egg back there. So I need work that gives me energy instead of draining it, especially heading into years where my health might not hand me the same runway it does now. Something that provides for Smidge and me for the long haul.
Now here's what I keep seeing out there. Almost all the advice runs on the same engine: do the least, charge the most, build the high-ticket offer that pulls in the people with money to spend.
So when I got told to add a zero to my Joy Prompt Club membership - take it from twenty-seven dollars a month to two hundred and seventy, then chase the high-ticket crowd - my first reaction was pure shock.
Because... all I do is three prompts a week and one live session where we shoot the sh!t, talk AI, and I help people with whatever they're stuck on. People are gonna pay me two hundred seventy dollars a month for THAT? I couldn't believe it.

My financial advisor (me, at 2am, doing math I do not understand) strongly recommended I take the money. I overruled her.
And then they kept talking, and I could see the shape of it. And I'll be honest with you - part of me was tempted. Really tempted. Because it would mean less work. Fewer people, more money, less of me spread thin. Let's not pretend that isn't appealing when your 401k has thirteen thousand dollars in it.
But the longer I sat with it, the more it felt extractive. It was me stepping right into the shape of everything I can't stand about the world right now. I've been through what I've been through. I've watched how many people are just surviving out there, trying to get by. And I'm gonna take my little piece off the top of that? Price out the exact people who need this most?
No. I can't sit with myself after that. That's not who I am.
Here's what I actually want to build. Things that give people joy. Things that make a woman look at her own life and see she has options. Opportunity. Possibility. I've been told that what I bring to a room is making people feel seen, feel safe, sparking something in them, making them feel brave. If that's the thing I get to give people - then f*** yes, I'm in. A business where I do that, that gives me energy, that I love, where people walk away with something real, and it puts a little good into the world while it pays my bills. That's the life I see. That's the twenty-year version.
So. Joy Prompt Club. Twenty-seven dollars a month. Staying right where it is.
Not because I couldn't use the money. Because the price is the promise. The day I add that zero is the day I've decided some of you don't get to come in - and I'm not building that.
That's all I had to say.
Radical remembering
Here's what I keep forgetting: somebody made all of this up. Nobody carved it into a stone tablet.
Add a zero. Ten-x your rates. Build the funnel, run the launch, post five times a day or the algorithm forgets you exist. It gets handed down like it's the law of gravity - this is how it's done, this is how it works.
But some person, somewhere, just did it that way once. It made them money. Everybody copied.
That's the entire origin story. A habit that put on a suit and started calling itself the rules.
Which means the pricing is yours to set. The hours, yours. What you sell, who you'll gladly take money from, who you flat-out refuse to price out - all of it, yours to make up.
Nobody who wrote the rulebook was any smarter than you.
So write your own.
Last week’s shenanigans
Four again this week. If you’re new here, this is where I share the stuffs I encountered on the interwebs that touch, move, inspire, or simply make me snort-laugh.
Seen
Nicole sent me this one, and I'm not gonna lie... I cried. It's like someone took a peek inside my actual experience and posted it. "For anyone that loves a woman with ADHD." If this is you - or you love someone living it - watch it.
I am worried
My musician friends call this "alternative lyrics" - where you take a classic GenX song and remake it in your own experience. This woman nails it. Two thumbs up. No notes.
Aggressive self love
A creator I just found (thanks, Marion!) who embodies - pun very much intended - exactly how I feel now about what I wear. It took me hitting my 50s to get here. I'd love to see the younger ones arrive with this much of it already loaded.
Folding chair
Another one where I felt fully seen. Thousands of reactions and shares, which means I'm not alone in it. And that's lovely.
This week’s freebie
Show It What Good Looks Like
You can describe what you want for an hour. Or you can show it one example and watch it click in ten seconds.
When I want captions that sound like me, I don't explain my voice. I paste in two of my own old posts and say: "Write three more like these. Same rhythm." It catches the beat off the examples better than off any description I could write.
Telling it "make it warm and witty" gets you a robot's idea of warm and witty. Showing it warm and witty - an actual thing you like - gets you the real article. Examples beat adjectives every time.
Now you. Find one thing whose sound you love. A text a friend sent that made you grin. A note you wrote that felt like you. A caption that made you laugh.
Paste it in and say: "Write me one like this, about [your thing]." Watch it borrow the rhythm instead of guessing at it.
Misses the mark? Point at the exact part. "Match the short sentences." "Keep it this dry." "Less polished, more like the example." You're not starting over. You're showing it the target again.

Show It What Good Looks Like
This is Lesson 6 of You're the Boss of This Thing, my new little course living inside Joy Prompt Club. Seven lessons, real moves, you set the pace. Come boss some bots around with us.
ROCO Prompt O’ the Week
Should I Though?
This week someone told me to add a zero. More money, less work. I ran it against what I'm building and said no.
But here's the trap I almost walked into, and the whole reason this prompt exists. It's real easy to turn EVERY piece of advice down and feel noble doing it. Raise your rates? No. Niche down? No. Post more? Absolutely not. And sometimes that "no" isn't your mission talking. It's fear in a good outfit.
So this one guards both doors. It checks whether the advice would betray what you're building - AND whether you're about to reject something smart just because it scares you. It asks five questions, including the two nobody wants to answer out loud: can you actually pay your bills on the path you're defending, and would you still say no if it didn't scare you one bit?
Answer honestly. Especially those two.
**Role:** Act as a sharp, honest advisor who wants me to still be in business in twenty years. You care about my mission AND my rent. You will not help me get talked into a model that betrays what I'm building - and you will not let me dress plain old fear up as "principles" to dodge a scary-but-smart move. Tell me the truth even when it costs me money, and even when it costs me my comfortable no.
**Objective:** Help me decide whether to take, reject, or reshape a specific piece of business advice I've been given. Base it on two things: whether the advice serves what I'm actually building, and whether I can survive the path I'm defending. Not just what makes the most money. Not just what feels safest.
**Context:** Interview me one question at a time. Do not dump them all at once. Ask, in this order:
1. What's the advice?
2. What am I actually building, and who is it for?
3. What would I have to give up or change to follow it?
4. Can I actually pay my bills on the path I'm defending? Push me for real numbers, not vibes.
5. If this advice had zero chance of failing and didn't scare me at all, would I still say no?
Wait for each answer before you ask the next. If I answer #4 with feelings instead of numbers, ask again. Once you have all five, do not read my answers back to me.
**Output:** Open with a one-line verdict
- take it, leave it, or reshape it. Then give me:
- Why, tied to what I told you I'm building.
- A straight read on my numbers: whether the path I'm defending actually keeps the lights on, or whether I'm being principled on a sinking ship.
- A straight read on the fear question: if my answer flipped once the fear came off, tell me plainly it was fear talking, not mission.
- If the verdict is leave it or reshape it, hand me the version of this advice I could actually say yes to - the true part worth keeping, minus the part that betrays me.
End with the single next thing I should do. No hedging, no "it depends," no both-sides.What happens next
You'll walk out with a verdict and one next step - take it, leave it, or the reshaped version you can actually say yes to. The advice was never the boss of you. This just helps you remember that.
The Scoop, The Skinny, The Lowdown
Three quick hits, every week. The Scoop: one AI word, decoded. The Skinny: one move you can steal today. The Lowdown: one tool, one honest verdict, from my own use. A word, a move, a verdict. In and out.
The Scoop
Sycophancy
Ask an AI if your plan is any good and watch it trip over itself telling you it's BRILLIANT. That's sycophancy - the AI's habit of agreeing with you because it's guessing that's what you want to hear. It's why "is this a good idea?" is a near-useless question. Ask it to poke three holes in your plan instead. It's not your yes-man unless you let it be.
The Skinny
Make it interview you.
Most people cram everything into one message and hope for the best. Try ending your prompt with this instead: "Ask me one question at a time until you have what you need, then answer." Now the AI's pulling the good stuff out of you instead of guessing at it. It's the whole engine behind the Should I Though? prompt up above - and it works on anything. Trip planning. A dreaded email. Any decision you keep circling.
The Lowdown
This week: Gamma
Gamma was one of the first single-purpose AI tools I actually put money down on, and I'm still paying happily. Here's the why: you type what you want, and it builds you a presentation that looks like you hired someone. If slides make you break out in hives - if you know your stuff cold but "make it look polished by Thursday" sends you into a spiral - this is the one.
You describe the deck (or paste in notes you already have), pick a look, and it lays the whole thing out for you. Not just slides, either. It'll spin the same brain-dump into a doc or a simple webpage.
Cost: free to start. You get 400 credits at signup, enough to build around ten decks and find out if you love it. Just know those free credits are one-and-done - they don't refill. Want to drop the little "Made with Gamma" badge? That's about $10 USD a month. The step up with your own branding and view analytics runs somewhere around $18-20. Prices are in USD and Gamma likes to fiddle with them, so peek at the live page before you commit.
One honest thing: when you export to PowerPoint, Gamma's stretchy card layout doesn't always squish neatly into regular slides. Budget five minutes of cleanup if you're handing the file off to someone else.
If polished-in-a-hurry is the job, Gamma's still one of the friendliest tools in the drawer.
What’s coming up
Stream with Emily, take 2

Em & Deb: Shoot the Sh!t (LIVE on LinkedIn)
Thursday, July 23 | 11:00-11:30 AM CDT
The job market is weird, so Emily Worden and I are going live for 30 minutes to say so out loud. No polished webinar. No 53-slide deck. No pretending any of this is normal. Just two humans talking job searching, AI, LinkedIn, visibility, and finding a little joy while everything feels like a lot. Bring your questions and your "what the hell is happening?" It's a teaser for Summer School, our workshop series for job seekers gearing up for the September Surge.
[RSVP here]
Coming in August - Prompt Along: AI Improv (monthly, evenings)
A new monthly one, and this time it's after dinner instead of mid-workday. Think part AMA, part watch-me-actually-use-the-tools. You throw out the questions, the ideas, the "can it even do this?" and I work them live while you play along at home. How it goes depends entirely on who's in the room - which is exactly the fun of it. Evenings, 7PM CDT, starting in August. I'm still pinning down the first date, so watch this spot, or hit reply and tell me you want in and I'll make sure you hear first.
That's it for this week.
So that's where I landed. $27 stays $27.
Not a stunt, not a strategy. It's just the one I could live with.
Your turn. Pick a rule somebody swears you have to follow - raise the price, niche down, post daily, whatever's been nagging you - and this week, don't. Do it your way and see what breaks. (Probably nothing.)
Then hit reply and tell me what you picked. That inbox is me. Always has been.
💜
Take care of yourself, take care of each other,
Deb
P.S. And yeah, I still sell things. The prompt kits at aiconfidential.net are the little ones - throw a few bucks at them if they'd make your week easier. Priced like a human.

